Windows 8 is the biggest Windows update in years, and it has IT people scrambling to decide whether to upgrade or wait to see how things unfold for other companies. For small businesses, the decision carries even more weight: according to a survey released by Staples in June 2012, 64 percent of small business owners perform their own IT and other network maintenance. That means if there are big glitches, small business owners are really going to feel the pain very directly to the bottom line. Despite that, the survey also found that of those who were aware of Windows 8, 70 percent had upgrade plans in place.

We decided to take to the streets and ask business owners whether they planned to upgrade to Windows 8 or wait. Here’s what they told us. (Learn the basics about this new OS in 10 Things You Need to Know About Windows 8.)


Andrew Schrage, founder and editor in chief at Moneycrashers.com

My business partner and I have already decided that, at least initially, we won't be upgrading to Windows 8. While the operating system seems to have many benefits, there are still some unanswered questions and other issues.

The biggest concern at the moment is cost. Many of the best Windows 8 features can only be enjoyed using a tablet computer, and many of our staff (myself included) still use a traditional desktop PC. The cost of upgrading everyone or purchasing additional tablets just isn't viable at the moment. (On that note, if we ever did migrate to tablet PCs, I'd give the iPad a serious look before considering a Windows-based device.)

We jumped on the Windows 7 bandwagon as soon as it came out and experienced a lot of issues. That's another reason we're holding off, at least for now. History has shown me that it's best to give new operating systems at least six months before completely migrating over. There are too many hiccups and issues that will inevitably arise.

David Handmaker, CEO of Next Day Flyers

We have about 100 work stations in our two facilities and have been testing Windows 8. The user interface is more than a bit awkward. By using the "Metro" UI, Microsoft tried to bring a "tablet-esque" experience to the PC. The standard "Start" icon, which for years has been in the lower left corner, is now brought to the user only in a hover state. Even the functionality used to shut the machine down is a little difficult to find, and there is an extra step involved in the process.

Overall it feels as if Windows 8 is a combination of two operating systems and the concern is the learning curve could disrupt our efficiencies. For now we’ll be skipping the upgrade. We’ll evaluate consumer reaction and perhaps revisit the subject six months or so after Microsoft launches the product.

Steven Holtzman, West Coast Aerial Photography Inc.

We're a small family business that specializes in aerial photography. Our industry is heavily tech-oriented, between the cameras, flight equipment and computers for post. We will be purchasing the Windows 8 upgrade (which is reportedly going to be $40/computer) and then waiting until many of the bugs are worked out and our vital programs are updated to take advantage of the new OS. We've made the mistake of jumping into new software before, and have lost countless hours to bugs, glitches and performance issues due to the migrations. This time, I think we will be holding off on the initial upgrade.

Jordan Rosenberg, founder of MyAgingFolks.com

I have upgraded all of our small team’s machines to the RTM WIN 8. We share a lot of documents back and forth and instead of working in Google Docs or using non-native Dropbox, we use Office with the baked in Skydrive.

An added plus is the way that Windows 8 manages profiles and personalization. Employees can switch among the laptops we use and by logging in, they can bring their settings with them.

Ken Kilpatrick, President of Sylvia Marketing & Public Relations

We are waiting to upgrade, yet eager to make the jump. Our public relations agency specializes in crisis management, so we rely on cutting-edge technology to support the rapid-fire operations necessary to serve our clients. There is no tablet, mobile device or cloud-based technology we won't look at and ultimately purchase if it adds even slight value to the service we provide. Windows 8 looks promising, but Microsoft has a reputation of creating disastrous operating systems after a great upgrade. Windows ME followed Windows 98, Vista followed XP. Each had rave reviews by those who got beta versions. As tempting as it is, we are going to wait. Too much is at stake.

Heinan Landa, CEO of Optimal Networks, a computer and network support services company for small and mid-sized businesses

If you need an operating system upgrade, we recommend upgrading to Windows 7 because the Windows 8 interface is dramatically different. Unless you are planning to standardize your office environment to Microsoft Surface tablets, the Windows 8 OS is not worth looking at for another six to 12 months. However, you should be making sure that you are eligible to receive licensing upgrades and, if you are purchasing new hardware, ensuring that it is compatible with Windows 8.